5-methylene-7-octen-1-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-methylene-7-octen-1-ol
• 英文别名: 5-Methylideneoct-7-en-1-ol
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: OEWNTKWFUIYYCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-己炔-1-醇 、 3-溴丙烯 在 氢化镓 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以51%的产率得到5-methylene-7-octen-1-ol
  参考文献：
  名称：

  Regioselective allylgallation of terminal alkynes

  摘要：

  终端炔烃与现场生成的烯丙基镓试剂（由镓和烯丙基溴化物反应生成）在THF中于70°C进行Markovnikov加成反应，得到相应的1,4-二烯，产率良好。

  DOI：

  10.1039/b417975g

文献信息

• Carboindation of Carbon−Carbon Triple Bonds:  Regioselective Indium-Mediated Allylation of Functionalized Alkynes and Transformation into Halogen-Substituted 1,4-Dienes
  作者：Ernst Klaps、Walther Schmid

  DOI：10.1021/jo9908593

  日期：1999.10.1

  By examining the allylindation of a series of substituted alkynes, the relationships between allylindation reactivity and alkyne structure were systematically investigated. While terminal alkynes with protected hydroxyl groups gave the corresponding allylated branched 1,4-dienes (Markovnikov products) within 5-6 h, the unprotected alkynols reacted markedly faster, requiring only 2-4 h of ultrasonication in THF to produce the 1,4-dienols in good yields. In the latter reactions, the regioisomeric outcome was found to depend on the distance between the hydroxyl group and the alkyne moiety: propargylic substrates gave linear 1,4-dienes (anti-Markovnikov products), suggesting the involvement of bicyclic "chelation-controlled" transition state, while 4-pentynol and higher homologues exclusively afforded the branched 1,4-dienes. Moreover, the proposed vinylic alpha,alpha-bis-indium intermediates from both protected and unprotected substrates were successfully quenched with N-bromosuccinimide (NBS) and N-iodosuccinimide (NIS) to form tri- and tetrasubstituted dienes in good yields. Taken as a whole, these results illustrate the remarkable stability of the allylindium and vinylindium intermediates despite the presence of protic functionalities in the reaction mixture.
• Regioselective allylgallation of terminal alkynes
  作者：Phil Ho Lee、Yunkiu Heo、Dong Seomoon、Sundae Kim、Kooyeon Lee

  DOI：10.1039/b417975g

  日期：——

  The reactions of terminal alkynes with allylgallium reagents generated in situ from gallium and allyl bromides gave the corresponding 1,4-dienes in good yield via Markovnikov addition in THF at 70 °C.

  终端炔烃与现场生成的烯丙基镓试剂（由镓和烯丙基溴化物反应生成）在THF中于70°C进行Markovnikov加成反应，得到相应的1,4-二烯，产率良好。